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4-(Diphenylamino)phenylboronic acid is an organic compound that features a boron atom bonded to a phenyl ring with a diphenylamino group attached to the 4-position. It is known for its strong multiphoton-excited blue photoluminescence and lasing properties, making it a valuable material in the field of organic electronics and photonics.

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  • 201802-67-7 Structure
  • Basic information

    1. Product Name: 4-(Diphenylamino)phenylboronic acid
    2. Synonyms: 4-(DIPHENYLAMINO)PHENYLBORONIC ACID, (CONTAINS VARYING AMOUNTS OF ANHYDRIDE),97.0%(T);4-(Diphenylamino)phenylboronic acid;4-(Diphenylamino)phenylboronic Acid (contains varying amounts of Anhydride);Triphenylamine-4-boronic Acid;4-Diphenylamino-phenylboronic acid or Triphenylami;4-(Diphenylamino)phe;4-(DiphenylaMino)benzeneboronic acid, 98%;Boronic acid, B-[4-(diphenylaMino)phenyl]- Boronic acid, [4-(diphenylaMino)phenyl]- (9CI)
    3. CAS NO:201802-67-7
    4. Molecular Formula: C18H16BNO2
    5. Molecular Weight: 289.14
    6. EINECS: N/A
    7. Product Categories: blocks;BoronicAcids;B (Classes of Boron Compounds);Boronic Acids;Triphenylamine series;white crystal powder;Phenylamine Series;Aryl;Boronic Acids;Boronic Acids and Derivatives
    8. Mol File: 201802-67-7.mol
  • Chemical Properties

    1. Melting Point: 110-115 °C
    2. Boiling Point: 484.52 °C at 760 mmHg
    3. Flash Point: 246.829 °C
    4. Appearance: /
    5. Density: 1.24 g/cm3
    6. Vapor Pressure: 0mmHg at 25°C
    7. Refractive Index: 1.665
    8. Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
    9. Solubility: soluble in Toluene
    10. PKA: 8.71±0.17(Predicted)
    11. CAS DataBase Reference: 4-(Diphenylamino)phenylboronic acid(CAS DataBase Reference)
    12. NIST Chemistry Reference: 4-(Diphenylamino)phenylboronic acid(201802-67-7)
    13. EPA Substance Registry System: 4-(Diphenylamino)phenylboronic acid(201802-67-7)
  • Safety Data

    1. Hazard Codes: N/A
    2. Statements: N/A
    3. Safety Statements: N/A
    4. WGK Germany: 3
    5. RTECS:
    6. HazardClass: N/A
    7. PackingGroup: N/A
    8. Hazardous Substances Data: 201802-67-7(Hazardous Substances Data)

201802-67-7 Usage

Uses

Used in Organic Electronics Industry:
4-(Diphenylamino)phenylboronic acid is used as a reagent for the preparation of push-pull arylvinyldiazine chromophores and benzothiadiazole-based fluorophores containing triphenylamine functionality. These chromophores and fluorophores are essential for developing blue light-emitting and hole-transporting materials for electroluminescent devices, such as organic light-emitting diodes (OLEDs) and organic photovoltaic cells.
Used in Dye-Sensitized Solar Cells:
4-(Diphenylamino)phenylboronic acid serves as an efficient sensitizer for dye-sensitized solar cells, enhancing their energy conversion efficiency and performance.
Used in Organic Synthesis:
4-(Diphenylamino)phenylboronic acid is utilized as a reagent in Suzuki coupling reactions, a widely used method for the formation of carbon-carbon bonds in organic synthesis. It is particularly useful in ligand-free Suzuki reactions, simplifying the process and reducing the need for additional ligands.
Used in the Production of Advanced Materials:
4-(Diphenylamino)phenylboronic acid is used in the synthesis of p-quaterphenyls laterally substituted with a dimesitylboryl group. These materials are employed as solid-state blue emitters, contributing to the development of next-generation eep-blue organic light-emitting devices (OLEDs) and Prange electroluminescent materials for single-layer white polymer OLEDs.
Chemical Properties:
4-(Diphenylamino)phenylboronic acid is a white to light green solid, indicating its stability and purity as a chemical compound.

Check Digit Verification of cas no

The CAS Registry Mumber 201802-67-7 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 2,0,1,8,0 and 2 respectively; the second part has 2 digits, 6 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 201802-67:
(8*2)+(7*0)+(6*1)+(5*8)+(4*0)+(3*2)+(2*6)+(1*7)=87
87 % 10 = 7
So 201802-67-7 is a valid CAS Registry Number.
InChI:InChI=1/C18H16BNO2/c21-19(22)15-11-13-18(14-12-15)20(16-7-3-1-4-8-16)17-9-5-2-6-10-17/h1-14,21-22H

201802-67-7 Well-known Company Product Price

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  • TCI America

  • (D3537)  4-(Diphenylamino)phenylboronic Acid (contains varying amounts of Anhydride)  

  • 201802-67-7

  • 1g

  • 490.00CNY

  • Detail
  • TCI America

  • (D3537)  4-(Diphenylamino)phenylboronic Acid (contains varying amounts of Anhydride)  

  • 201802-67-7

  • 5g

  • 1,680.00CNY

  • Detail
  • Alfa Aesar

  • (H52902)  4-(Diphenylamino)benzeneboronic acid, 98%   

  • 201802-67-7

  • 250mg

  • 533.0CNY

  • Detail
  • Alfa Aesar

  • (H52902)  4-(Diphenylamino)benzeneboronic acid, 98%   

  • 201802-67-7

  • 1g

  • 1705.0CNY

  • Detail

201802-67-7SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 11, 2017

Revision Date: Aug 11, 2017

1.Identification

1.1 GHS Product identifier

Product name [4-(N-phenylanilino)phenyl]boronic acid

1.2 Other means of identification

Product number -
Other names Triphenylamine-4-boronic Acid

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:201802-67-7 SDS

201802-67-7Relevant articles and documents

A single 2-(2′-hydroxyphenyl)benzothiazole derivative can achieve pure white-light emission

Cheng, Jinling,Liu, Di,Bao, Lijun,Xu, Kai,Yang, Yang,Han, Keli

, p. 3215 - 3220 (2014)

The synthesis and photophysics of two novel 2-(2′-hydroxyphenyl)- benzothiazole (HBT) derivatives are presented. The electron-withdrawing trifluoromethyl (CF3) group in compound 1 facilitates the deprotonation of the phenolic hydroxy group. Well-resolved triple fluorescence from the enol, keto, and phenolic anion, which ranges from 350 to 600 nm, was detected for 1 in ethanol, which marks the first time triple fluorescence from an excited-state intramolecular proton transfer (ESIPT) molecule has been reported. Both triphenylamine and CF3 were introduced into derivative 2. Intramolecular charge transfer and the "red-edge effect" resulted in the bathochromic shift of dual fluorescence of 2. Triple fluorescence was also observed for 2 in ethanol. In mixed acetonitrile and ethanol, pure white-light emission with CIE coordinates of (0.33, 0.33) and a quantum yield of 0.25 was achieved for 2. This work provides a new avenue for the rational design of an ESIPT molecule to achieve white-light generation under mild conditions.

An AIE active monoimidazolium skeleton: High selectivity and fluorescence turn-on for H2PO4- in acetonitrile and ClO 4- in water

Gao, Chao,Gao, Ge,Lan, Jingbo,You, Jingsong

, p. 5623 - 5625 (2014)

We disclose herein a monoimidazolium skeleton 1 with an aggregation-induced emission (AIE) characteristic. This fluorogenic skeleton exhibited high selectivity and fluorescence turn-on for H2PO4- in acetonitrile and ClO4- in water. the Partner Organisations 2014.

Synergy between twisted conformation and effective intermolecular interactions: Strategy for efficient mechanochromic luminogens with high contrast

Yuan, Wang Zhang,Tan, Yeqiang,Gong, Yongyang,Lu, Ping,Lam, Jacky W. Y.,Shen, Xiao Yuan,Feng, Cunfang,Sung, Herman H-Y.,Lu, Yawei,Williams, Ian D.,Sun, Jing Zhi,Zhang, Yongming,Tang, Ben Zhong

, p. 2837 - 2843 (2013)

A strategy towards efficient mechanochromic luminogens with high contrast is developed. The twisted propeller-like conformations and effective intermolecular interactions not only endow the luminogens with AIE characteristics and high efficiency in the crystalline state, but also render them to undergo conformational planarization and disruption in intermolecular interactions upon mechanical stimuli, resulting in remarkable changes in emission wavelength and efficiency. Copyright

Oxidative C-H Homocoupling of Push-Pull Benzothiazoles: An Atom-Economical Route to Highly Emissive Quadrupolar Arylamine-Functionalized 2,2′-Bibenzothiazoles with Enhanced Two-Photon Absorption

Fakis, Mihalis,Georgiou, Dimitris,Gyepes, Róbert,Hrobárik, Peter,Nociarová, Jela,Osusky, Patrik,Polyzos, Ioannis,Smolí?ek, Maro?

supporting information, p. 5512 - 5517 (2021/07/31)

Copper(II)-catalyzed C-H/C-H coupling of dipolar 2-H-benzothiazoles end-capped with triphenylamine moieties affords highly fluorescent 2,2′-bibenzothiazoles with quadrupolar (D-π-A-π-D) architecture displaying large two-photon absorption (TPA) cross sections (543-1252 GM) in the near-infrared region. The notably higher TPA performance as compared to quadrupolar π-systems with a widely used 2,2′-bipyridine core, along with the ease of the synthesis and chelating N^N ability, makes the title biheteroaryl platform an attractive building block for a large scope of functional dyes exploiting nonlinear optical phenomena.

Arylamine organic electroluminescent compound and preparation method thereof, and organic electroluminescent device

-

Paragraph 0052; 0060; 0061; 0118; 0126; 0127, (2021/07/01)

The invention discloses an arylamine organic electroluminescent compound. The arylamine organic electroluminescent compound is characterized in that a constitutional formula of the compound is as described in the invention. A preparation method for the co

New compounds and organic light-emitting diode including the same

-

Paragraph 0200-0206; 0314; 0321-0326, (2019/08/30)

PURPOSE: A compound is provided to improve luminous efficiency and to make low voltage operation possible when applied to an organic electroluminescence device by having low driving voltage and excellent luminous efficiency. CONSTITUTION: A compound is represented by chemical formula 1. In chemical formula 1, each R is selected from hydrogen, deuterium, substituted or unsubstituted C1-6 alkyl, substituted or unsubstituted C7-30 alkyl, substituted or unsubstituted C3-30 cycloalkyl, substituted or unsubstituted C5-30 cycloalkenyl, substituted or unsubstituted C1-30 alkoxy, substituted or unsubstituted C6-30 aryloxy, substituted or unsubstituted C1-30 alkylthioxy, substituted or unsubstituted C5-30 arylthioxy, substituted or unsubstituted C1-30 alkylamine, substituted or unsubstituted C5-30 arylamine, substituted or unsubstituted C5-50 aryl, substituted or unsubstituted C3-50 heteroaryl, substituted or unsubstituted silicon, substituted or unsubstituted boron, substituted or unsubstituted silane, carbonyl, phosphoryl, amino, nitrile, hydroxy, nitro, halogen, amide, and ester.

Highly efficient dual-core derivatives with EQEs as high as 8.38% at high brightness for OLED blue emitters

Kang, Seokwoo,Jung, Hyocheol,Lee, Hayoon,Park, Sunwoo,Kim, Joonghan,Park, Jongwook

, p. 14709 - 14716 (2019/12/06)

Three blue fluorescent materials were newly synthesized by attaching triphenylamine side groups at their ortho, meta, and para positions to a dual core moiety of anthracene and pyrene, two chromophores with good luminous efficiency; these three materials were 2-(6-(10-(2-(diphenylamino)phenyl)anthracen-9-yl)pyren-1-yl)-N,N-diphenylaniline (o-TPA-AP-TPA), 3-(6-(10-(3-(diphenylamino)phenyl)anthracen-9-yl)pyren-1-yl)-N,N-diphenylaniline (m-TPA-AP-TPA), and 4-(6-(10-(4-(diphenylamino)phenyl)anthracen-9-yl)pyren-1-yl)-N,N-diphenylaniline (p-TPA-AP-TPA), respectively. The optical, thermal, and electroluminescence (EL) properties of the synthesized materials were measured. All three materials were found to be real blue emitters in the solution state and display high PLQY values. A device doped with p-TPA-AP-TPA displayed a very high efficiency of 9.14 cd A-1 and an EQE of 8.38% at a high luminance of 5000 cd m-2.

1,2,4-thiadiazole compound, preparation method and application thereof

-

, (2019/02/04)

The invention discloses a 1,2,4-thiadiazole compound, a preparation method and an application thereof. The 1,2,4-thiadiazole compound used as a light emitting layer material of an OLED device is capable of obviously promoting the performances of the device, such as luminous intensity, current efficiency, power efficiency, external quantum efficiency and chroma and is capable of prolonging the service life of the device.

1,2,4-thiadiazole compound, preparation method and application thereof

-

, (2019/02/04)

The invention discloses a 1,2,4-thiadiazole compound, a preparation method and an application thereof. The 1,2,4-thiadiazole compound used as a light emitting layer material of an OLED device is capable of obviously promoting the performances of the device, such as luminous intensity, current efficiency, power efficiency, external quantum efficiency and chroma and is capable of prolonging the service life of the device.

Pyrimido-isoindole derivative and organic light-emitting device with same

-

, (2018/03/09)

The invention discloses a pyrimido-isoindole derivative and an organic light-emitting device with the same. The organic light-emitting device comprises a cathode, an anode and one or a plurality of organic matter layers. The organic matter layers are positioned between the cathode and the anode, and at least one of the organic matter layers comprises the pyrimido-isoindole derivative. The pyrimido-isoindole derivative and the organic light-emitting device have the advantages that the pyrimido-isoindole derivative has large conjugation systems and is high in hole mobility and good in hole transport performance; the pyrimido-isoindole derivative is good in heat stability and solubility and favorable for material film formation; the organic light-emitting device with the pyrimido-isoindole derivative used as the corresponding organic matter layer only requires low driving voltages and is high in light-emitting efficiency and light-emitting brightness and long in service life.

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